The Hard Part with Evan McCann

Mark Goad is the GM of Canada at Alan.The health partner who prevents, insures, and cares daily - Alan's mission is a healthier humanity.Alan is partnered with 30,000 companies, has more than 700,000 members, is at +€470m ARR with 600 employees in France, Spain, Belgium and now Canada.Takeaways- Choosing to pursue business over a CFA.- His move and time in venture.- Career decision-making.- His role as Board Chair of CAMH Engage.- How the Alan opportunity came about.- Why he wanted to join a French company entering the Canadian market.- Working with regulators. - Working for a global organization but also localizing the offering and product for Canada.- Understanding the Canadian market's nuances is key.- Innovation in healthcare.- Direct billing.- Their launch customer segment and why that focus.- Community engagement and building awareness.- Unique traits of Alan's culture, operations and day-to-day.- Hiring strategies.- Transforming insurance and the purchasing experience.Chapters00:00 The Entrepreneurial Spirit: Early Beginnings06:01 Navigating Career Decisions: Embracing Risk12:04 Joining Alan: A Unique Opportunity in Healthcare18:03 Localizing Healthcare: Adapting to the Canadian Market25:27 Building a Strong Community Presence31:27 Transforming Insurance Purchasing Experience37:16 Engaging with Startups EffectivelyKeywordsentrepreneurship, venture capital, career decisions, mental health, healthcare innovation, regulatory challenges, Canadian market, startup culture, risk management, insurance industry, insurance, direct billing, customer experience, startup culture, healthcare, community engagement, hiring strategies, technology integration, market entry, mental health

Simon De Baene is the Co-Founder and CEO of Workleap.Workleap is for HR teams that need to solve HR challenges. They help you make your people happier and more productive with the easiest employee experience technology to launch, manage and love. Takeaways- Why the name Gsoft was inspired by G-Unit.- Starting Gsoft (now Workleap) at 20 years old right out of school- Transitioning from a service company to a product company.- Building products allows for more control over destiny.- The decision to shut down the service side to focus on products.- Raising the first external capital from CDPQ after 19+ years.- Maintaining passion for close to 20 years.- Working half his life on Workleap.- Achieving $150M in revenue.- Major rebrand to WorkLeap and how to do that well.- The impacts of AI in the HR space.- Building company culture.- Why you can't be everything to everyone.- The importance of embracing change and letting go of nostalgia.- Building and staying in Montreal.- His one regret in building Workleap, not surrounding himself with advisors and mentors earlier.Chapters00:00 The Genesis of Gsoft: A Young Entrepreneur's Journey05:09 Transitioning from Service to Product: The Birth of Sharegate13:22 Navigating Growth: The Dual Product Strategy16:18 Capital Efficiency and the Decision to Raise Funds22:21 Maintaining Passion: A Lifelong Commitment to Workleap26:44 Rebranding: From Gsoft to Workleap27:18 The Evolution of Branding and Identity29:57 Navigating Workplace Changes and AI Integration34:53 Building and Scaling Company Culture40:00 Leadership Lessons and Personal Growth43:52 Proudly Building in Montreal49:01 Personal and Professional AspirationsKeywordsGsoft, Workleap, entrepreneurship, product development, service company, Sharegate, OfficeVibe, capital efficiency, rebranding, workplace tools, branding, workplace changes, AI, company culture, leadership, Montreal, entrepreneurship, personal growth, remote work, product development

Great to dive into Build Canada with Daniel Debow!Build Canada is a platform of bold ideas for growth, innovation, and prosperity. Every policy is proposed by successful Canadian entrepreneurs with deep knowledge from building in the relevant areas. They are supported by policy experts with experience in government. Their singular focus is a Canada where people build again.Takeaways- What is Build Canada? Why did it start? Why now?- How did the team actually get Build Canada out of the group chat?- Fostering economic growth in Canada.- Why memos? Why that format?- The team of volunteers driving Build Canada.- Diversity in voices is crucial for comprehensive policy discussions.- Criticism of the initiative.- Creating positivity and actionable change.- Encouraging builders to speak up.- Courage is essential for public discourse and change.- Direct communication versus traditional media.- Diving into the product and systems behind Build Canada.- Why a bipartisan approach?- Building a community around shared values.- A love for one's country can inspire action and change.Chapters00:00 Introduction to Build Canada02:51 The Format and Purpose of Policy Memos06:08 Diversity of Voices in Policy Memos08:48 Team Dynamics and Volunteer Commitment12:06 Addressing Criticism and Misconceptions14:59 Creating Positivity and Actionable Change18:02 Encouraging Builders to Speak Up21:07 Courage to Speak Up22:37 The Power of Direct Communication23:41 Building Canada: A Digital Revolution25:14 Bipartisan Approach to Policy29:19 Engaging with Government and Public Policy35:21 Personal Motivations Behind Build Canada38:33 Looking Ahead: Future Projects and PassionsKeywordsBuild Canada, public policy, entrepreneurship, policy memos, Canadian growth, volunteer organization, builders, economic change, policy ideas, community engagement, Canada, public policy, entrepreneurship, Build Canada, digital communication, government engagement, bipartisan, courage, personal motivation, community

Kat Garcia is the Co-Founder and Co-CEO of Ground.Uncover untapped revenue, with zero effort. Ground is an AI revenue driver growing the next generation of consumer companies, for Founders, Agencies, and Go-to-Market Teams.Takeaways- Kat's time at BCG Digital Ventures.- Understanding customer psychology.- Retention strategies and how Ground helps.- Growth teams face unprecedented challenges currently.- Integrating with existing tools.- AI models leveraging product, customer, and browsing data.- Ground helps businesses drive revenue without changing teams.- Insights from AI can inform better product decisions.- Personalization is now achievable due to AI.- New York's tech scene.KeywordsAI, entrepreneurship, growth marketing, BCG Digital Ventures, revenue generation, retention strategies, tech founder, e-commerce, product development, market trends, AI, customer journey, e-commerce, personalization, marketing, technology, consumer behavior, retention, insights, business growth

Anson Yu and Hudhayfa (HudZah) Nazoordeen, co-hosts of Socratica, discuss their unique initiative fostering interdisciplinary collaboration among creatives. They share how Socratica was born as a countercultural response to post-COVID isolation, emphasizing community ownership and personal agency. The duo explains the concept of 'permission' that allows members to explore diverse interests freely. They outline the structured sessions and emerging community nodes, highlighting the critical role of alumni and the evolving symposium in maintaining vibrant connections.

Mark Ang is the Co-Founder and CEO of GoBolt.Takeaways- GoBolt started as Second Closet, focusing on student storage.- Their TTC ad which got them a great ROI.- The pivot to GoBolt involved a complete rebranding and change in the business model.- Building trust with customers is crucial in logistics.- Nuances in the 3PL space.- Last mile logistics. - Integrating technology + human operations.- Determining how and when to launch new markets/cities.- Why account management is still a business function that Mark owns.- How GoBolt seeks to be a partner with their clients.- Innovative capital strategies to enhance efficiency. - Consumer expectations for delivery speed. Is it the same day? Next day? Two days?- Why GoBolt uses EV delivery trucks, not just because of environmental reasons.- Building proprietary software to optimize logistics operations.- Compartmentalizing setbacks can help maintain focus and progress.Chapters00:00 The Early Days of GoBolt05:09 The Pivot: From Second Closet to GoBolt09:22 Understanding the 3PL Landscape13:25 Optimizing Last Mile Logistics19:01 Merging Technology with Human Operations25:00 Market Expansion Strategies28:09 Innovative Capital Strategies in Logistics33:17 The Evolution of Delivery Speed Expectations37:26 The Shift to Electric Vehicles in Logistics41:37 Focus and Discipline in Business Growth46:02 Building a Resilient Company CultureKeywordsGoBolt, Second Closet, 3PL, logistics, e-commerce, market expansion, last-mile delivery, startup journey, business pivot, trust in logistics, logistics, capital strategies, delivery speed, electric vehicles, business growth, company culture, innovation, efficiency, entrepreneurship, technology

Jean Schmitt is the Managing Partner of Jolt Capital.Jolt Capital is a private equity firm specializing in investment in growth capital technology.Jolt Capital generates returns for its investors by enabling growth-stage technology-rich companies with strong fundamentals to execute their scaling strategies, in sectors that offer strong exit potential across hardware-driven or software-driven solutions: photonics, advanced materials, cybersecurity, electrification, smart sensors, semiconductors, personalized health, and more.They provide growth capital to their portfolio companies (from €10M to €50M in tranches).Takeaways- Misconceptions and realities of deep tech.- The returns that can happen in deep tech.- Investing in deep tech requires a long-term commitment and patience.- Sourcing investments in deep tech often involves identifying strong IP.- How to identify what strong IP looks like.- Evaluating deep tech companies.- Why the focus on later-stage companies.- Why Jolt is excited about Canada's deep tech scene.- Playbook for scaling deep tech companies with leadership and sales.- Jolt's first investment in Canada.- Dynamics and breakdown of the European tech market.Chapters00:00 The Genesis of Jolt and Deep Tech Investment05:06 Misconceptions and Realities of Deep Tech09:44 Investment Strategies in Deep Tech15:07 Sourcing and Evaluating Deep Tech Companies19:53 Trends and Market Dynamics in Deep Tech25:02 Geographical Focus: Europe and Canada29:58 First Steps in the Canadian Market34:58 Building and Scaling Deep Tech Companies40:01 Learning from Global Investment PracticesKeywordsJolt, deep tech, investment strategies, intellectual property, market trends, Canada, Europe, technology companies, venture capital, growth stage

Jelena Djuric is the Co-Founder and CEO of Noble.Noble is changing how stablecoins and other real world assets are issued on blockchains by combining minimalistic, high security architecture with the cross-chain efficiencies of the IBC protocol.Takeaways- Jelena's political science and economics background shaped her interest in crypto.- Background on Stablecoins.- Providing infrastructure for stablecoin issuance and transactions.- The market for stablecoins has exploded, reaching a valuation of $220B.- Noble's protocol is designed to support various stablecoins across different blockchains.- The $1B Stripe acquisition of Bridge signifies mainstream interest in stablecoin infrastructure.- Why Robinhood and many others are launching Stablecoins.- The concept of "App Chains".- The Cosmos model allows for application-specific blockchains, enhancing performance and sovereignty.- Noble's infrastructure leverages existing open-source protocols.- The crypto space is evolving with various business models, including transaction fees and token representation.- User experience - making stablecoins feel like traditional money.- Fundraising in the crypto space.Chapters00:00 Journey into Crypto: A Unique Background03:12 The Rise of Stablecoins: A New Financial Paradigm05:57 Noble's Role in the Stablecoin Ecosystem08:48 The Future of Stablecoins: Diversity and Innovation11:56 Speed and Efficiency: The Promise of Stablecoins15:00 The Concept of App Chains and Noble's Vision27:04 Understanding Blockchains and Noble's Approach29:23 Technical Infrastructure and Engineering Challenges33:38 Business Models in the Crypto Space37:05 The Future of Stablecoins42:06 Trust in Crypto and Financial Systems44:17 Funding and Growth Strategies45:58 Personal Insights and Future AspirationsKeywordscrypto, stablecoins, blockchain, governance, financial technology, digital currency, Noble, Ethereum, Bitcoin, decentralized finance, blockchain, stablecoins, crypto, Noble, Cosmos, business model, trust, funding, technology, engineering

Jean-Michel Lemieux has an incredible profile. Former VP of Engineering at Atlassian Former CTO at Shopify Founder of DevDegree at Shopify Restaurant owner of Arlo in Ottawa Author of an upcoming book "Build Right Side" Founder of SeaPeopleTakeaways- Early Ottawa tech scene.- Moving to Australia to work for the iconic company Atlassian.- Building trust when leading a new team.- Being a product expert as a CTO is key.- Moving back to Ottawa and joining Shopify.- Scaling Shopify's engineering team from 50 to 3,000.- Work with Founders as an executive like Tobi at Shopify and Mike and Scott at Atlassian.- JML's take on Founder Mode.- Background behind DevDegree.- JML's take on effective communication as a leader.- A strong opinion on technology tools is essential as a CTO.- Launching and starting Arlo one of Canada's top 100 restaurants.- Similarities behind starting a restaurant and tech.- Building a boat and JML's plan to tackle a massive sailing trip.- Power of writing and his book.- SeaPeople, one of his latest ventures.Chapters00:00 The Early Ottawa Tech Scene02:23 Career Trajectory and the Move to Atlassian05:15 Lessons from Atlassian08:03 Transition to Shopify10:50 Scaling Teams at Shopify15:44 Working with Founders18:58 The Concept of Founder Mode21:24 DevDegree: Bridging Education and Industry24:25 Traits of a Modern CTO26:33 Optimizing Technology Teams for Speed and Efficiency27:43 The Intersection of Food and Technology: Starting a Restaurant29:42 Navigating Life After Shopify: A Personal Journey31:36 Exploring the Seas: Building a Boat and Community34:07 Finding Product-Market Fit: Lessons from Entrepreneurship37:20 Writing as a Passion Project: Insights from Building a Book39:04 Embracing a Growth Mindset in Business and Life41:10 The Sneaker Phenomenon: Unexpected Lessons from Shopify47:22 Looking Ahead: Personal and Professional AspirationsKeywordsOttawa tech scene, Atlassian, Shopify, tech leadership, founder relationships, scaling teams, DevDegree, modern CTO, technology, CTO, product design, entrepreneurship, restaurant, growth mindset, Canada, sailing, community, product-market fit

Ian Burgess is the President and CTO of Validere Technologies.Validere is an Emissions Management Software Platform that enables customers to integrate their operational and field measurement data for regulatory reporting and corporate emissions initiatives.Over 50 of North America’s leading energy companies rely on Validere’s technology and multidisciplinary experts to understand their emissions and navigate an increasingly complex environment with clarity and ease.Takeaways- Ian's background in physics.- The journey to product-market fit took longer than expected.- YC significantly influenced Ian's entrepreneurial perspective.- Emissions reporting.- Re-architecting the product for scaling.- Proximity to clients enhances business development efforts.- Energy companies face challenges when adopting new technologies.- High-touch service for happy clients.- Gen AI adds complexity to data management.- Ian's thoughts on raising.- Reflections on 10 years of building Validere.- It's hard to hire someone who is strong where you're weak.- Success is the time average of your successes and failures.- Early days of Pioneer Fund and angel investing.Chapters00:00 From Physics to Tech: Ian's Journey05:04 Lessons in Product Market Fit13:35 Re-architecting for Success19:19 Navigating Sales in the Energy Sector25:51 Adapting to GenAI and Client Needs32:39 The Importance of a Diverse Investor Base38:17 Reflections on a Decade of Entrepreneurship45:46 The Shift to Audiobooks and Learning51:21 Finding Balance in Hard TimesKeywordstech startup, emissions reporting, product market fit, Y Combinator, energy sector, measurement science, software development, client relations, generative AI, business strategy, Generative AI, team composition, investor base, CTO, entrepreneurship, change management, Pioneer Fund, audiobooks, personal growth, work-life balance